J. Nat. Prod. 2004, 67, 1650-1653 Steroids and Sesquiterpenoids from the Soft Corals Dendronephthya...
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Transcript of J. Nat. Prod. 2004, 67, 1650-1653 Steroids and Sesquiterpenoids from the Soft Corals Dendronephthya...
![Page 1: J. Nat. Prod. 2004, 67, 1650-1653 Steroids and Sesquiterpenoids from the Soft Corals Dendronephthya gigantea and Lemnalia cervicorni Chang-Yih Duh, Ali.](https://reader036.fdocuments.us/reader036/viewer/2022062320/56649d4b5503460f94a28e71/html5/thumbnails/1.jpg)
J. Nat. Prod. 2004, 67, 1650-1653
Steroids and Sesquiterpenoids from the Soft Corals Dendronephthya gigantea and
Lemnalia cervicorni
Chang-Yih Duh, Ali A. H. El-Gamal, Pei-Ying Song, Shang-Kwei Wang and Chang-Feng Dai
Department of Marine Resources, National Sun Yat-sen University, Kaohsiung, Taiwan ,
Department of Microbiology, Kaohsiung Medical University, Kaohsiung, Taiwan ,
and Institute of Oceanography, National Taiwan University,Taipei, Taiwan, Republic of China
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A Photo of Dendronephthya soft coral
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Abstract
One new cytotoxic steroid, dendronesterone A (1), two new steroids, dendronesterones B and C (2 and 3), and a known steroid (4) were isolated from the methylene chloride solubles of the Formosan soft coral Dendronephthya gigantea. Two cytotoxic ylangene-type sesquiterpenoids, lemnalol (5) and the new compound cervicol (6), as well as two ylangene-type sesquiterpenoids, isolemnalol (7) (a new compound) and 4-oxo-R-ylangene (8), were isolated from the methylene chloride solubles of the Formosan soft coral Lemnalia cervicorni. Their structures were elucidated by 1D and 2D NMR spectral analysis, and their cytotoxicity against selected cancer cells was measured in vitro.
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Aim of StudyAim of Study
Aim of study is focused on the separation of bioactive substances from marine organisms, the Formosan soft corals Lemnalia cervicorni (Nephtheidae) and Dendronephthya gigantea (Nephtheidae) were studied because the CH2Cl2 extracts showed significant cytotoxicity to A549 (human lung adenocarcinoma), HT-29 (human colon adenocarcinoma), and P-388 (mouse lymphocytic leukemia) cell cultures as determined by standard procedures. Bioassay-guided fractionation of CH2Cl2 extracts of D. gigantea resulted in the isolation of one new cytotoxic steroid, dendronesterone A (1), two new steroids, dendronesterones B and C (2 and 3), and a known steroid (4).
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Bioassay-guided fractionation of CH2Cl2
extracts of L. cervicorni resulted in the isolation of two cytotoxic ylangene-type sesquiterpenoids, lemnalol (5) and a new compound, cervicol (6), as well as two ylangene-type sesquiterpenoids, isolemnalol (7) (a new compound) and 4-oxo-R-ylangene (8).
Aim of StudyAim of Study
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Extraction, Separation and purification Scheme for Extraction, Separation and purification Scheme for soft coral soft coral Dendronephthya giganteaDendronephthya gigantea
Bodies of the soft coral Dendronephthya gigantea were freeze-dried to give 1.88 Kg of a solid
extract with CH2Cl2 (4lX3), conc in vacum
14.2 g of CH2Cl2 extract
CC, Sil. gel using n-hex. and n-hex. -EtOAc gradient, followed byEtOAc-MeOH% of EtOAc /n-hex
10% 17%
1*,2* 3*,4*
HPLC (Rp-18), MeOH-H2O (93:7)
HPLC (Rp-18), MeOH-H2O (93:7)
Sub Fr.. A Sub Fr.. B
* ED50 9.84, >100, >100, 8.93 g/ml respectively against P-388 cytotoxic cell line* ED50 >100, >100 >100 and 9.03 g/ml respectively against HT-29 cell line
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O
Dendronesterones B (2)
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O
Dendronesterones A (1)
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O
Dendronesterones C (3)
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O
(4)
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Compounds Isolated from Dendronephthya gigantea
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1
1H NMR of Dendronesterone A (1)
2 22,23
182627
19
21
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COSY spectrum Dendronesterone A (1)
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O
1 22223
1
2
22,23
1826 27
1921
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(HSQC Dendronesterone A (1
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O
1 22223
1
22
232
14,179
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HMBC Dendronesterone A (1)
1 2 22
23
3
1
23222
4
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HNMR of Dendronesterone B (2)
1
12 28
X
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FABMS of Dendronesterone B (2)
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O m/z 396 C28H44O
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1HNMR Dendronesterone C (3)
12
42223
182626
2119
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COSY spectrum Dendronesterone C (3)
1 2 42223
1
24
22,23
12
3
45
67
8
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O
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DEPT Experiment of Dendronesterone C (3)
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7615 11
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2119
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HMBC Experiment of Dendronesterone C (3)
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1 2 42223
5
1
222
234
17 149
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HSQC Expermint of Dendronesterone C (3)
3
5
1
222
23,4
1 2 42223
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17,149
182627
21
19
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Expanded HMBC of Dendronesterone C (3)
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19 21 2627
18
17 149
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FABMS of Dendronesterone C (3)
m/z 381 (M++1) C27H40O
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1HNMR of Dendronesterone D (4)
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O
O
1 2
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O
O
13C NMR of Dendronesterone D (4)
1 2322
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Expanded 13C NMR of Dendronesterone D (4)
14 179
20 5
134
2312
10 824 7
256
16
15
2627
1121 19 18
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Expanded COSY of Dendronesterone D (4)
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O
O
HSQC of Dendronesterone D (4)
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Expanded HSQC of Dendronesterone D (4)
14 17 920 513 1819211126
271525
616
72481023124
18
26,2719
21
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O
O
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HMBC of Dendronesterone D (4)
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Bodies of the soft coral Lemnalia cervicorni were freeze-dried to give 0.42 Kg of a solid
extract with CH2Cl2 (3lX3), conc in vacum
37.1 g of CH2Cl2 extract
CC, Sil. gel using n-hex. and n-hex. -CH2Cl2 gradient, followed byCH2Cl2-EtOAc, gradientn-hex/CH2Cl2
(1:3)
Compound 7* Compounds 5*,6*
CC, Sil. gel using n-hex.-EtOAc(47:3)
Sub Fr.. ASub Fr.. C
* ED50 16.3, >50, >50, and >50 g/ml respectively against P-388 cytotoxic cell line* ED50 10.5, >50 >50 and >50 g/ml respectively against HT-29 cell line
(0:100)
Sub Fr.. B
Compounds 7*,8*
CH2Cl2/EtOAc(1:1)
.
CC, Sil. gel using n-hex.-CH2Cl2 (49:1)
CC, Sil. gel using n-hex.-acetone (99:1)
Extraction, Separation and purification Scheme for soft coral Lemnalia cervicorni
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OH
1
2 3
4
5
67
8
9
1110
12
13
14
15
Lemnalol (5)
1
2 3
4
567
8
9
1110
12
13
14
15
Cervicol (6)
OH
1
2 3
4
567
8
9
1110
12
13
14
15
OH
Isolemnalol (7)
1
2 3
4
567
8
9
1110
12
13
14
15
4-oxo- ylangene (8)
O
Compounds Isolated from Lemnalia cervicorni
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2D INADAQUATE of lemnalol
OH
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2 3
4
5
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1110
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